Studies on the Photochemical Rearrangements of Enantiomerically Pure, Polysubstituted, and Variously Annulated Bicyclo[2.2.2]octenones

Qiao Yan; Benoit Bolte; Yuhua Bai; Martin G. Banwell; Anthony C. Willis; Paul D. Carr

doi:10.1021/acs.joc.7b01243

Studies on the Photochemical Rearrangements of Enantiomerically Pure, Polysubstituted, and Variously Annulated Bicyclo[2.2.2]octenones

Qiao Yan, Benoit Bolte, Yuhua Bai, Martin G. Banwell^*, Anthony C. Willis, Paul D. Carr

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

A series of enantiomerically pure bicyclo[2.2.2]octenones, including the lactone-annulated system 26, has been prepared by engaging derivatives of an enzymatically derived and homochiral cis-1,2-dihydrocatechol in inter- or intra-molecular Diels-Alder reactions. Systems such as 26 readily participate in photochemically promoted oxa-di-π-methane rearrangement or 1,3-acyl migration processes to give products such as diquinane 34 or mixtures of cyclobutanone 36 and cyclopropane 38, respectively.

Original language	English
Pages (from-to)	8008-8022
Number of pages	15
Journal	Journal of Organic Chemistry
Volume	82
Issue number	15
DOIs	https://doi.org/10.1021/acs.joc.7b01243
Publication status	Published - 4 Aug 2017

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abstract = "A series of enantiomerically pure bicyclo[2.2.2]octenones, including the lactone-annulated system 26, has been prepared by engaging derivatives of an enzymatically derived and homochiral cis-1,2-dihydrocatechol in inter- or intra-molecular Diels-Alder reactions. Systems such as 26 readily participate in photochemically promoted oxa-di-π-methane rearrangement or 1,3-acyl migration processes to give products such as diquinane 34 or mixtures of cyclobutanone 36 and cyclopropane 38, respectively.",

author = "Qiao Yan and Benoit Bolte and Yuhua Bai and Banwell, {Martin G.} and Willis, {Anthony C.} and Carr, {Paul D.}",

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AU - Yan, Qiao

AU - Bolte, Benoit

AU - Bai, Yuhua

AU - Banwell, Martin G.

AU - Willis, Anthony C.

AU - Carr, Paul D.

PY - 2017/8/4

Y1 - 2017/8/4

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AB - A series of enantiomerically pure bicyclo[2.2.2]octenones, including the lactone-annulated system 26, has been prepared by engaging derivatives of an enzymatically derived and homochiral cis-1,2-dihydrocatechol in inter- or intra-molecular Diels-Alder reactions. Systems such as 26 readily participate in photochemically promoted oxa-di-π-methane rearrangement or 1,3-acyl migration processes to give products such as diquinane 34 or mixtures of cyclobutanone 36 and cyclopropane 38, respectively.

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DO - 10.1021/acs.joc.7b01243

M3 - Article

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SP - 8008

EP - 8022

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

Studies on the Photochemical Rearrangements of Enantiomerically Pure, Polysubstituted, and Variously Annulated Bicyclo[2.2.2]octenones

Abstract

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